What My Experience as a Crossdressing Married Man has Taught Me About Gender

My wife always claimed that she could gauge my emotional state by looking in the laundry basket; when I was anxious, she said, I was more likely to find me dressed in drag.
Nothing was hidden from Lee. It wasn’t a big deal, so I told her about it right after we met. However, it wasn’t something I told her about either. What this meant, I couldn’t even begin to guess.

A friend’s confession that they cross-dress would have been accepted by me without question. If you’re the one experiencing it, though, things change.

As a rule, I didn’t enjoy dressing in a manner inconsistent with my gender. Only about six pairs of pants, a few nightgowns, and two dresses made up the entirety of my female wardrobe back then. Wearing male underwear (pants) as part of a cross-dressing act was the norm rather than the exception. Yet, there was still a question that made me uneasy: Why did I feel compelled to go there?

I never felt like I belonged with the boys when I was a kid. Even though I had a decent amount of physical prowess, I was always known as the smart, geeky kid in school. However, the term “f*ggot” was used to refer to me. Several trips to the dictionary yielded no results for me. That it was meant for me became obvious quickly enough.

Even as a child, I was the school’s token “effeminate” boy. A female friend of my mother’s would often comment that they wished they had hair like mine because it would look so good on a woman. I was even told that, if I were a woman, I would have beautiful legs.
The rumors that I was gay spread by the other boys were unfounded. They said I acted too femininely.

My best friends were always girls, all the way through high school and college. In part, this was a moral dilemma. There were very few men in my life who treated women with any kind of respect. I found that the casual and open misogyny that was prevalent, especially in groups, was too much to bear.

On the other hand, the women in my life possessed empathy and sensitivity. Talking was not a contest but a means of connecting with one another. Also, they genuinely sympathized with the general populace. They had an inclination toward humanity.
I never felt more out of place among a group of men than when I was an adult, and that includes being among a group of Buddhist monks.

The reason I was never “one of the guys” was because I never identified as a male. Although I had suspected as much, it was only when I was able to concentrate on the issue that I realized how right I had been.

After being locked up for forty years or so, my feminine self was released, and she went completely crazy. It would not be in public, but rather private. I began shopping for women’s clothing and became preoccupied with discussing my internalized transgender experiences. Both Lee and I were overwhelmed by the intensity and pace of the situation, and we eventually skidded to a halt.

Lee was concerned that I would reveal my trans identity and immediately start a medical transition she was not prepared for. The fact that she ignored my reassurances made me very frustrated. After a particularly heated argument, I decided to store all of my feminine garments in the basement one morning.

If it was the only thing that could kill me, I would go out like a man.

Among cross-dressers, a “purge” of that nature is fairly typical. For me, however, the root cause was less embarrassment and more bewilderment. I’d done a lot of reading on the web. Everything I could find, from blogs to support forums to academic papers. None of the things I was reading, however, jibed with my own observations.

I didn’t identify as transgender because I didn’t think of myself as either male or female. I wasn’t bigender; there was only one of me; there was no sexism or transgenderism. I didn’t identify as neither a man nor a woman, so I couldn’t be considered androgynous.
I couldn’t quite put my finger on it, but I had a sense of being neither male nor female. The challenge was working out what this meant for me personally and professionally.

All aspects of me, from my core beliefs and interests to my overall character, were already a hybrid of stereotypically male and female traits. But I knew I had to take action to care for my femininity, honor it, and express it, and a shift in my wardrobe was the first and most natural place to start.

Yet, why? Isn’t that simply buying into a cultural narrative about what it means to be feminine? As for the gender binary, what exactly do we mean when we say “male” or “female”?

The consensus amongst gender theorists is that genders are social categories defined by the expectations placed upon those who are assigned to them, typically at birth. You act this way if you have a vagina; that way if you have a penis.

But a mythology that gives gender a false objectivity obscures its true nature: The concept of gender has its roots not only in society but also in biology. Women have evolved to be nurturers, while men are programmed to sow their fields. Gender norms in society are thus portrayed as inevitable and not merely acceptable.

But gender norms vary greatly, both historically and geographically. Although there is a biological component to gender, the binary gender categories recognized in American society are the result of cultural and political processes.

When one considers the extreme improbability of gender norms and expectations, it can be puzzling that anyone could ever feel at ease with them.

However, one does not merely acquire a predetermined gender. As a result of one’s upbringing, most people are able to confidently adopt the role that is expected of them. Most dissidents eventually conform because they fear social consequences if they don’t.
But there are still dissenters. Too many facets of one’s identity are affected by one’s gender assignment and assigned norms and expectations for it to be otherwise.

Therefore, when I say that I don’t consider myself to be a man, what I mean is that the social expectations placed on me because of my perceived gender make me uncomfortable. There’s this thing called “being treated like a man,” and I definitely don’t want that.
All of us can relate to this type of thing. Lee frequently has to remind the bartender that she wants Coke, not diet, when she orders a Jack and Coke. However, this disconnection occurs more frequently and more profoundly in my case.

Too much of my life has been spent listening to people mock and insult me because of my femininity. What was wrong with that? I was labeled a male, put under pressure to act like one, and ultimately found myself falling short.

There’s more, and it gets worse. Nowadays, a woman can act more “masculinely” (including by donning traditionally male clothing) than a man would who prefers the feminine aesthetic.

I don’t understand why that is the case. Simply put: In today’s culture, being feminine is seen as a weakness. Any woman who aspires to the best by adopting traditionally male behaviors is admirable (even if it is not rightly hers). When men start behaving in stereotypically feminine ways, they bring shame on themselves.

In any case, I’m sticking two fingers up to all that nonsense by enthusiastically embracing the gender roles that society assigns to women. I disagree with the supposition that vaginitis automatically makes a person “feminine.” A time when we can all be who we truly are is something I long for. However, if a woman feels the need to express her “femininity,” whether just for the day or all the time, she certainly has the right to do so.

That also includes the male gender. Wearing makeup or nail polish is not “unworthy” of a man, and neither is liking feminine clothing or accessories.

So, I’m taking my time and giving my decisions more consideration. Though Lee has been very encouraging, we aren’t exactly itching to find out what would happen if I wore a pink floral sweater to the mall. Though we’ve been honest with our daughter, not even our closest friends know the truth about me just yet.

As of right now, I’m operating in stealth mode. I use a male identity when I’m out in public, but I still like to dress in women’s clothes. A cursory examination would fool you into thinking otherwise. Except when I’m flying or visiting the doctor, I always wear a pair of pants that matches the rest of my outfit. I prefer to wear a camisole or women’s tank top under my T-shirt in the winter. I wear mostly women’s clothing, with the exception of a few men’s shirts and a few pairs of shorts. This is because I am tall and it is difficult to find tops that are long enough.

I frequently don knee highs and the occasional pair of hose or tights because I adore the feminine feel and lovely designs of women’s socks. I even have a pair of women’s loafers that pass as European men’s shoes so I can wear them to the office without being mocked.
My friend Lee helped me find a great clear mascara, and I have several lipsticks that are sheer enough to blend in with my lips. On my fingers and toes in the summer, I wear either clear or very subtly tinted nail polish. As a result, I now present as much more feminine than I used to.

When I’m at home, I put on whatever I want, which can range from girly jeans to a skirt or dress. Beautiful pajama bottoms and soft pink pj tops. Wear a pair of classic pumps, strappy sandals, or adorable flats. The earrings were too big and dangly. Makeup that fits the bill.

Not so much that I’ve changed on the inside, but there is something very therapeutic about expressing my emotions.

It’s a powerful feeling to finally be able to look at myself in the mirror and see the woman I always knew was there, and to not be ashamed of her but to embrace and love her. And it’s great.